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Updated: Feb 22, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
3-Cyanoallyl boronates are versatile building blocks in the synthesis of polysubstituted thiophenes
Wenjie Shao1, Sherif J Kaldas1, Andrei K Yudin1
1Davenport Research Laboratories , Department of Chemistry , University of Toronto , 80 St. George St. , Toronto , ON M5S 3H6 , Canada .
Abstract:
We report the preparation of hitherto unprecedented 3-cyanoallyl boronates using condensation of the parent α-boryl aldehyde and nitriles. The resulting allyl boronates have been used to generate a wide range of borylated thiophenes, which represent a valuable class of heterocycles in modern drug discovery. Subsequent Suzuki-Miyaura cross-coupling enabled the synthesis of pharmaceutically important 3,5-disubstituted aminothiophenes. Moreover, late stage functionalization gave access to borylated bromothiophene and thieno[2,3-b]pyridines.
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